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  • Writer's pictureShana Antonissen

Planning a Bareboat Catamaran Charter - Greece Dodecanese Islands

Updated: Aug 21, 2023

When Mike and I decided to plan a trip to Greece, we wanted to try something completely new. This led us to book a bareboat catamaran to explore some less traveled islands—a whole new kind of trip for me to research and plan. Preparing for a new experience can be a bit overwhelming. How do I deal with it? Breaking it into manageable tasks helps me stay organized and reduce stress. This blog will take us through the steps in my process.

Greek Island Groups
Map of Greek Island Groups. Credit: Dimosthenis Vasiloudis / GreekReporter

Step 1 - Location Research

We knew we wanted to go to Greece, but where in Greece is an even bigger question. With around 6,000 islands and islets in Greece, scattered across different regions, we had plenty of options to choose from. Below is a short rundown of the major island groups.

The most popular island groups are:

Cyclades: Known for their iconic blue-domed churches and white-washed buildings, the Cyclades islands are situated in the central part of the Aegean Sea. Some notable islands include Mykonos, Santorini, Paros, Naxos, and Ios.

Ionian Islands: Located off the west coast of Greece, the Ionian Islands are known for their lush green landscapes and clear blue waters. Key islands include Corfu, Kefalonia, Zakynthos, and Lefkada.

Dodecanese: Situated in the southeastern part of the Aegean Sea, these islands have a mix of historical sites and beautiful beaches. Popular islands in this group are Rhodes, Kos, Patmos, and Symi.

Saronic Islands: Closest to Athens, the Saronic Islands offer a more tranquil escape. Some notable islands are Aegina, Hydra, Poros, and Spetses.

Northeastern Aegean Islands: These islands are located in the northeastern part of the Aegean Sea, closer to Turkey. Some islands in this group are Lesbos, Samos, and Chios.

Sporades: Situated to the northeast of the Cyclades, the Sporades islands offer a mix of verdant landscapes and charming villages. Skiathos, Skopelos, and Alonissos are among the main islands.

Crete: The largest Greek island, Crete, is located south of the mainland. It has a diverse landscape, rich history, and distinctive culture.

Aegean Islands: This is a broader category that includes various smaller island groups like the aforementioned Cyclades, Dodecanese, and Sporades.

Each group has its own unique charm and attractions. The choice of which region and islands to visit depends on your interests. If you're looking for vibrant nightlife and iconic views, the Cyclades might be a good fit. If you prefer a mix of historical sites and picturesque landscapes, the Dodecanese could be a great choice. If you're interested in exploring ancient history and natural beauty, the Ionian Islands could be ideal. And if you want a more serene and less crowded experience near Athens, the Saronic Islands could be a good option.

Step 2 - Pricing & Availability

Armed with the breakdown of the different island groups, I dove into researching boat availability and pricing. Travel tip: Pricing goes down after the high-summer season for most Mediterranean destinations (after September 1st).

Mike and I had decided to go for a catamaran instead of a monohull sailboat. Catamarans ticked all the right boxes for us – they offered better stability, speed, space, comfort, and safety, even in rough weather. Plus, their shallow draft allowed us to get closer to the shore for better anchoring and unique views. I looked into catamarans ranging from 40 to 50 feet in length in each island group between the end of August and the first two weeks of September. Taking into account factors like the quality of the boats, their availability, and the cost, we eventually narrowed down our choices. Our final decision pointed to the Dodecanese islands, with Kos being the starting point for our week of sailing.

Step 3 - Charter Booking

You always want to ensure you use a reputable charter company. I went with Sailology to book our bareboat Lagoon 42". Since neither Mike nor I have an ICC certification, we decided to include a skipper for our trip. The charter company helped us arrange this. But remember, when you have a skipper on a bareboat charter, you need to provide food not just for your group but also for the skipper.

The charter company is your main contact to discuss any special requirements you might have for the catamaran, such as equipment, amenities, and crew (if applicable). We put down half of the charter cost to confirm the reservation, with the remaining half due one month before the charted embarkation date. There are some final fees due and a security deposit to handle at the marina when we check-in. These final fees include the final cleaning fee, the addition of wifi for the boat, provisions, and early embarkation.

Here is a look at what comes with our boat

Lagoon 42

4 Double cabins w/attached water closet

2 Single cabins




What do I mean by bareboat? Bareboat technically refers to any boat that can be chartered without a skipper, provisions, or crew, but typically, bareboating refers to sailing yachts, including monohulls and catamarans.

Step 4 - Airline Booking

Since we usually take a fall trip to visit my father in the Netherlands, we decided to combine this sailing trip with our fall visit. I have done quite a bit of research on how to get the most out of my points and miles, and I finally got to put it to use for this trip. We used 120,000 American Express points to transfer into Virgin Airlines miles plus $180 to book our round-trip tickets from MSP to AMS. I was happy to find a non-stop round-trip flight from Schipol Airport in Amsterdam to Kos with Transavia Airlines. Granted, our flight leaves at five something in the morning, but early morning is better than a flight with layovers, in my opinion.

Step 5 - Hotel Booking

Kalimera Mare Hotel

We're flying into Kos on the same day we start our charter, so we didn't need to book a hotel before we set sail. However, we figured it would be a good idea to spend a night in Kos when we get back, just to get used to being on land again after a week at sea. I found a nice small hotel called Kalimera Mare. It has 9 suites and 35 rooms, and it's on the south side of Kos Island in the village of Kardamaina. This will give us some time to check out the cool stuff on Kos Island, like the Agia Barbara church, Agioi Anargyroi, and the really pretty Virgin church before we head out on our flight the next day.

Step 6 - Provisioning

Provisioning involves the important task of preparing and obtaining the necessary items for your trip, such as food, drinks, and supplies. Depending on the charter company you're using, they might offer assistance in this area. Our plan was to have five planned dinners and leave a few nights open for dining onshore. To make this happen, I created a detailed shopping list for five people. The list covered non-perishable goods, ingredients for our planned meals, fresh produce, snacks, beverages, and cooking essentials.

Provision list

Since my sister and her partner are joining us on the journey, we all contributed ideas for meals that can be easily prepared in the boat's kitchen while we're at sea. Cooking responsibilities will be shared among us during the trip. As you're putting together your provisioning list, it's important to consider the dietary preferences and restrictions of everyone in your group. I sent the provisioning list to the charter company two weeks before our departure date. They will take care of purchasing everything and loading it onto the boat at the marina, so we're all set when we arrive.

Our Sailing Menu

Step 7 - Packing

Packing for a catamaran trip requires a bit of strategy due to limited storage space onboard. We are fortunate enough to have an extra cabin, so I could bring along all of the fun goodies to make our trip relaxing and enjoyable. I am packing lightweight and versatile clothing that can be layered for changing weather conditions. Don't forget swimwear, sun protection (hats, sunglasses, sunscreen), comfortable shoes with non-marking soles, and any necessary medications. Since you'll be on the water, a waterproof bag can be handy for protecting valuables. Also, consider packing a beach towel, snorkeling gear, and entertainment options like books or games.

Throughout this process, communication is key. Stay in touch with the charter company, accommodation providers, and anyone else involved in your trip to ensure everything is on track. Or better yet contact me via the Request a Quote page and let me do all the organizing for you! And of course, don't forget to capture the excitement and memories of your adventure!

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